(1S,15R,16S,20R)-16-methyl-17-oxa-3,13-diazapentacyclo[11.8.0.02,10.04,9.015,20]henicosa-2(10),4,6,8-tetraen-18-ol

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (1S,15R,16S,20R)-16-methyl-17-oxa-3,13-diazapentacyclo[11.8.0.02,10.04,9.015,20]henicosa-2(10),4,6,8-tetraen-18-ol
• 化学式: C₁₉H₂₄N₂O₂
• 分子量: 312.412
• InChiKey: RXNUWTKSTOHKNN-QKCKJDOCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  23
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  48.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1S,15R,16S,20R)-16-methyl-17-oxa-3,13-diazapentacyclo[11.8.0.02,10.04,9.015,20]henicosa-2(10),4,6,8-tetraen-18-ol 在 盐酸 作用下， 反应 12.0h， 生成 19α-hydroxy-19β-methyl-18-oxayohimbane
  参考文献：
  名称：

  Men, Jean Le; Zeches, Monique; Sigaut, Francoise, Heterocycles, 1982, vol. 19, # 10, p. 1807 - 1812

  摘要：

  DOI：
• 作为产物：
  描述：

  萝巴新 在 盐酸 、 氢氧化钾 作用下， 以 甲醇 为溶剂， 反应 4.0h， 生成 (1S,15R,16S,20R)-16-methyl-17-oxa-3,13-diazapentacyclo[11.8.0.02,10.04,9.015,20]henicosa-2(10),4,6,8-tetraen-18-ol
  参考文献：
  名称：

  Men, Jean Le; Zeches, Monique; Sigaut, Francoise, Heterocycles, 1982, vol. 19, # 10, p. 1807 - 1812

  摘要：

  DOI：

文献信息

• Synthesis of ajmalicine derivatives using Wittig-Horner and Knoevenagel reactions
  作者：Ahcène Boumendjel、Jean-Marc Nuzillard、Georges Massiot

  DOI：10.1016/s0040-4039(99)01921-8

  日期：1999.12

  2-(2,3,4,9-Tetrahydro-1H-β-carbolin-1-yl)acetaldehyde, synthesized from tryptamine in five steps, is easily homologated by Wittig-Horner or Knoevenagel reactions to substituted acrylates. These highly reactive compounds are key intermediates in the synthesis of analogs of the natural indol alkaloid ajmalicine.

  用五步步骤从色胺中合成的2-（2,3,4,9-四氢-1 H -β-咔啉-1-基）乙醛很容易通过Wittig-Horner或Knoevenagel反应同化为取代的丙烯酸酯。这些高反应性化合物是天然吲哚生物碱阿兹玛林类似物合成中的关键中间体。
• Evaluation of Immunochemical Drug Screenings of Whole Blood Samples. A Retrospective Optimization of Cutoff Levels after Confirmation-Analysis on GC-MS and HPLC-DAD
  作者：Lars Kroener、Frank Musshoff、Burkhard Madea

  DOI：10.1093/jat/27.4.205

  日期：2003.5.1

  Four commonly used immunoassay kits were evaluated for their efficiency in screening for drugs of abuse in whole blood. Six groups of illicit drugs (opiates, cannabinoids, amphetamines, cocain and benzoylecgonine, benzodiazepines, and methadone) were determined by using the homogenous assays ADx and CEDIA DAU and compared with the results produced by means of the inhomogenous assays MTP and Pyxis 24. The measured 86 blood samples were taken from authentic routine analyses between February and September, 2000. Chromatographic confirmation analyses were carried out in all cases (positive and negative immunochemical pretesting). The cutoff levels were retrospectively optimized to reduce false-negative results with priority. Furthermore, false-positive pretests were minimized in order to decrease laboratory work under economical aspects. Specificity and sensitivity were determined for each parameter and assay. For the ADx assay, specificities of 54% (cannabinoids) to 97% (cocaine and metabolite) and sensitivities of about 67% (amphetamine class) to 94% (opiates) were found. The CEDIA assay revealed specificities of 77% (methadone) up to 100% (benzodiazepines) and 75–96% sensitivities for amphetamines and opiates. The MTP immunoassay resulted in specificities of 52% (methadone) to 95% (opiates, cocain, and metabolite) and sensitivities of 92% (amphetamines) up to 100% (methadone). The evaluation of the Pyxis 24 resulted in specificities of 70–96% (benzodiazepines and amphetamines) and sensitivities of 75% (amphetamines) up to 100% (cannabinoids and methadone), respectively. In conclusion, the microtiterplate immunoassays revealed higher sensitivities and have proved to be at an advantage detecting the lowest concentrations of drugs. However, especially for clinical applications in emergency cases with acute intoxications, when screening results are urgently required, homogenic assays such as ADx or Cedia provide preferable alternatives with faster and easier handling.

  对四种常用免疫测定试剂盒筛查全血中滥用药物的效率进行了评估。使用同源检测试剂盒 ADx 和 CEDIA DAU 测定了六类非法药物（阿片剂、大麻类、苯丙胺、可卡因和苯甲酰可待因、苯并二氮杂卓和美沙酮），并与非同源检测试剂盒 MTP 和 Pyxis 24 的结果进行了比较。所测得的 86 份血样是 2000 年 2 月至 9 月间通过真实的常规分析采集的。对所有病例（免疫化学预检阳性和阴性）都进行了色谱确认分析。为了优先减少假阴性结果，对临界值进行了回顾性优化。此外，还尽量减少了假阳性预检，以减少实验室的经济工作量。确定了每个参数和检测方法的特异性和灵敏度。对于 ADx 检测法，特异性为 54%（大麻类）至 97%（可卡因和代谢物），灵敏度约为 67%（苯丙胺类）至 94%（阿片剂）。CEDIA 分析法的特异性为 77%（美沙酮）至 100%（苯二氮卓类），对苯丙胺类和阿片剂的灵敏度为 75%至 96%。MTP 免疫测定的特异性为 52%（美沙酮）至 95%（阿片剂、可卡因和代谢物），灵敏度为 92%（苯丙胺）至 100%（美沙酮）。对 Pyxis 24 进行评估的结果是，特异性分别为 70%-96%（苯二氮卓和安非他明），灵敏度分别为 75%（安非他明）至 100%（大麻类和美沙酮）。总之，微孔板免疫测定的灵敏度较高，在检测最低浓度的药物方面具有优势。不过，特别是在急性中毒的紧急临床应用中，当急需筛查结果时，ADx 或 Cedia 等同源检测法提供了更快更简便的替代方法。
• Chemical transformations of ajmalicine: structure and stereochemistry of some interchangeable transformation products
  作者：Asima Chatterjee、Suchitra Bandyopadhyay

  DOI：10.1021/jo00137a016

  日期：1982.7
• <b>Rauwolfia Alkaloids. XXXVIII.</b>¹ <b>Stereospecific Degradations Leading to the Absolute Configurations and Structures of Ajmaline, Sarpagine and Corynantheidine</b>²
  作者：M. F. Bartlett、R. Sklar、W. I. Taylor、E. Schlittler、R. L. S. Amai、Peter. Beak、N. V. Bringi、Ernest. Wenkert

  DOI：10.1021/ja00863a024

  日期：1962.2
• Men, Jean Le; Zeches, Monique; Sigaut, Francoise, Heterocycles, 1982, vol. 19, # 10, p. 1807 - 1812
  作者：Men, Jean Le、Zeches, Monique、Sigaut, Francoise

  DOI：——

  日期：——